Avoiding the Common Pitfalls of Strategy Offsites

Avoiding the Common Pitfalls of Strategy Offsites

There are three common types of strategy offsites. Here’s how to ensure they’re successful.

Offsite, onsite-offsite, retreat: whatever you call it, strategy and planning season is here! Your leaders and teams want to get back together and collaborate in person. Now is the time to co-create, to share, and to get alignment on your strategy.

Having supported and delivered dozens of offsites over the years, we hear about some common problems in previous offsites time and time again:

  1. Inviting guest speakers who are interesting, but whose content doesn’t serve a clear purpose;
  2. Planning to work through the past year’s challenges or blockers, but finding that attendees aren’t comfortable admitting failure in front of their peers or leaders; and,
  3. Aiming to generate alignment on the strategy moving forward, but instead surfacing more misalignment.

How do you avoid these common pitfalls, and design an offsite that will set you up for success? Let’s dig into why common approaches can backfire, so you can avoid experiencing an offsite pitfall.

1. The ‘Inspired-Thinking’ Strategy Offsite

Common Pitfall:
In this style of offsite, guest speakers are brought in and external research is shared to encourage attendees to get inspired by what is happening in the marketplace and to stretch their thinking when it comes to building their own strategies. However, external speakers can induce a ‘what was the point of that?’ feeling.

To avoid an overwhelming jumble of information, ensure that teams understand that the guest speaker is there to inspire, not to define strategy. These types of sessions are best served to set an overall vision and next steps.

Offsite Considerations:

  • Limit the objective: Provide your guest speaker with clear guidance about the challenges your business is facing and the themes you believe might inspire fresh thinking. It’s critical that your speaker connects their content to the overarching vision of your offsite.
  • Have an MC: This person can ensure a smooth ‘run of show’ for the day, coordinate all the speakers, and help make the content cohere and your objectives advance.
  • Don’t surprise your team: All team members should know that the speaker is there to bring in new insights for discussion—not to develop your new strategy. People need time to ruminate on fresh thinking. Post-speaker conversations should focus on thinking bigger and having a unifying vision, and not about immediately applying findings to strategy development.
  • Work across conventional boundaries: Form cross-functional teams after hearing the fresh thinking, and get them to workshop and co-create ways the new knowledge might fit with your business. This gets people applying new knowledge in a low-stakes way, and also works to break down organizational silos.

Offsite Outcomes:
Teams come away feeling inspired with relevant content that they can reflect on while developing strategic plans for their part of the business.

2. The ‘Show-and-Tell’ Strategy Offsite

Common Pitfall:
‘Show-and-tell’ sessions are common in organizations that have different lines of business (LOBs). These sessions bring together the separate LOBs to share their respective strategies. The thinking is that, by virtue of sharing, all teams will be better enabled to support one another and support the overall goal.

The real challenge, however, is that these different LOBs often work independently. That independence can’t be turned into collaboration in just one session. Furthermore, building a cohesive strategy means sharing in past successes and failures, but without structure and safety, these sessions sometimes feel combative.

Offsite Considerations:

  • Set a unifying goal: Your team members won’t benefit if, once they present their strategy, the rest of the attendees simply poke holes in it. Make an effort to bring teams closer together, and thus their strategies closer together, by setting a common mission, vision and goals for the organization (or recommunicating them, if they have already been set). Pre-offsite, LOBs should build their strategies with that unifying goal in mind.
  • Break down silos: Now that you have everyone clear on a unifying goal, you can use it to break down silos. When teams come together for the offsite, evaluation of peers’ strategies is on the basis of a common objective and not divergent ones. The intent shifts from ‘poking holes’, to supporting one another in advancing toward that shared vision.
  • Avoid perfection: Communicate the timeline and objective in advance, so teams know the ‘show-and-tell’ is only one part of the strategy-building process. Not having to make things final and ‘perfect’ for the show and tell takes the pressure off of teams. You can go further by encouraging them to speak about the parts of their strategy for which they would like guidance or support.
  • No showing off: These types of sessions can often be interpreted as an opportunity to show off successes. But real value in these sessions comes when teams can learn from one another’s mistakes, misdirections, attempted solutions. Have leaders model vulnerability by sharing their own mistakes and encouraging others to feel they can do the same.

Offsite Outcomes:
Teams go into the session feeling less stressed about ‘selling’ their strategy internally. With that, they can also come out of it feeling like they got the support and guidance they needed to finalize their strategic contribution to the business and vision.

3. The ‘We Need Everyone to Agree’ Strategy Offsite

Common Pitfall:
These types of sessions are usually about getting senior leadership and their management teams, or leadership and their board, to agree so that the business can move forward. The intention is generally to co-create the strategy together. Unfortunately, there are often misaligned objectives between the parties. This kind of offsite aims to ensure everyone’s point of view has been taken into account, but the result is often a strategy that is a clumsy compromise between several parties, rather than a strategy that has a clear purpose and focus.

Offsite Considerations:

  • Stakeholder interviews: Before the offsite takes place, have a central person or persons interview members of management, leadership or the board to understand their challenges and their conception of success. That way, the offsite objective and agenda can reflect back the unifying commonalities, and enable attendees to work together to resolve their differences.
  • Have a guiding light: Ensure that all parties are clear on the business vision, objectives, and underlying research. When there is disagreement, trying to resolve the differences can lead to an impasse. Rather, using the vision, objective and research can provide the foundational elements needed to prioritize through the disagreement.
  • Build in transparency: Misalignments can often come from a lack of knowing what others are doing. To create transparency, share pre- and post-session notes and conclusions in a format that everyone can access and build upon. We’ve seen the collaborative whiteboard Miro used well for sharing and collaborating on notes.
  • Celebrate agreement: It may not be possible to get all parties to agree on every element of the strategy, but where alignment is achieved should be celebrated. This support and acknowledgement is critical to moving forward and driving execution.

Offsite Outcomes:
Teams will feel less fatigued trying to break through differences, and more aligned thanks to the pre-work.

If you are about to host your first offsite, or you’re feeling rusty because some time has passed since your last offsite, we would love to help! To chat through your strategy offsite plans, book a call to connect.

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